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Cinchona-derived prolinamide in Brønsted acidic ionic liquids: A novel and recyclable catalytic system for asymmetric aldol reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
53303 46962 2016 6 PDF Available
Title
Cinchona-derived prolinamide in Brønsted acidic ionic liquids: A novel and recyclable catalytic system for asymmetric aldol reaction
Abstract

•Chiral prolinamide in Brønsted acidic ILs was firstly used in aldol reaction.•Good to high yields and ee were achieved for aldol reaction of aromatic aldehydes.•ILs were identified as Brønsted acid additives for aldol reaction.•Brønsted acidic ILs were beneficial to the enhancement of catalyst stability.•Prolinamide catalyst in Brønsted acidic ILs could be reused four times.

Cinchonine-derived prolinamide in Brønsted acidic ionic liquids was utilized for the first time as a novel and recyclable catalytic system for the asymmetric direct aldol reaction of acetone with aromatic aldehydes. The effects of the Brønsted acidity and amount of ionic liquid, co-solvents, catalyst amount, and reaction temperature on the catalytic activity and enantioselectivity were studied in detail. Good to high yields and ee values were achieved for the aldol reaction of various aromatic aldehydes with neat acetone in 1-methylimidazolium tetrafluoroborate ([Hmim]+BF4−) in the presence of 10 mol% of catalyst at room temperature. [Hmim]+BF4− was also identified as a Brønsted acid additive for the reaction and beneficial to the enhancement of catalytic performance. Moreover, the enhanced interaction between prolinamide and acidic ionic liquid facilitated the recoverability and reusability of organocatalyst. The catalyst recycling experiments indicated that there was only a slight loss in activity and enantioselectivity after four runs.

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Keywords
Asymmetric aldol reaction; Brønsted acidic ionic liquid; Organocatalysis; Prolinamide
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Cinchona-derived prolinamide in Brønsted acidic ionic liquids: A novel and recyclable catalytic system for asymmetric aldol reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Today - Volume 264, 15 April 2016, Pages 109–114
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us